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1,8-Diazabicyclo(5.4.0)undec-7-ene → N-[2-(2,6-Dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-acetamide

HRID 9952
ノート
印刷プレビュー

反応式

HRID 9952 の反応式
N12CCCN=C1CCCCC2.CO[C:14](=[O:30])[C:15]1[C:16](=[C:21]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[CH:22]=[CH:23][CH:24]=1)[C:17]([O:19]C)=O.Cl.[NH2:32][CH:33]1[CH2:39][CH2:38][C:37](=[O:40])[NH:36][C:34]1=[O:35]>CN(C=O)C>[O:35]=[C:34]1[CH:33]([N:32]2[C:17](=[O:19])[C:16]3[C:15](=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:25][NH:26][C:27](=[O:29])[CH3:28])[C:14]2=[O:30])[CH2:39][CH2:38][C:37](=[O:40])[NH:36]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 210401323-(Acetylamino-methyl)-phthalic acid dimethyl ester

生成物 1

HCID 9880527N-[2-(2,6-Dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-acetamide収率 22.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide
溶媒

反応条件

温度
120 °C

実験手順

1,8-Diazabicyclo[5,4,0]undec-7-ene (0.93 g, 6 mmol) was added dropwise to a stirred suspension of 3-(acetylamino-methyl)-phthalic acid dimethyl ester (1.61 g, 6.0 mmol) and aminoglutarimide hydrochloride (1.0 g, 6.0 mmol) in DMF (15 ml). The mixture was then heated to 120° C. for 24 hours. The cooled mixture was concentrated in vacuo and the residue was stirred with water (25 ml) and dichloromethane (20 ml). The resulting slurry was filtered to give 0.45 g (22%) of the product as a gray solid. Recrystallization from methanol gave a white solid: mp 177–179° C.; 1H NMR (DMSO-d6) δ (11.02 (s, 1H), 8.36 (t, J=5.8 Hz, 1H), 7.74–7.55 (m, 3H), 5.05–4.98 (dd, J=5.3 and 12.5 Hz, 1H), 4.57 9D, j=5.9 Hz, 2H), 2.84–2.70 (m, 1H), 2.51–2.34 (m, 2H), 1.95–1.91 (m, 1H), 1.79 (s, 3H); 13C NMR (DMSO-d6) δ (172.85, 169.89, 169.81, 167.56, 167.05, 139.37, 134.83, 133.35, 131.58, 127.14, 121.94, 48.91, 37.84, 30.98, 22.54, 22.05; Anal. Calcd. For C16H15N3O5+0.96 water: C, 55.45; H, 4.92; N, 12.12. Found: C, 55.27; H, 4.82; N, 12.00.

後処理

  1. concentrationThe cooled mixture was concentrated in vacuo
  2. filtrationThe resulting slurry was filtered

出典と根拠

ORDレコード
ord-7104d6d60d7c4909895bb7a01f22a534
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091353B2

反応ノート

読み込み中…

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